I just started with buildium it’s ok so far but my big concern it’s all cloud based which is good and bad, do I own that data are only own it if I keep paying?

It is far better if the landlord just lets Tina out of her lease, and accepts Sam as a new tenant.Or, the landlord might let Tina out of her lease, accept Sam as a new tenant, but also require Tina to guarantee Sam's lease for the final six months (using my example) of Tina's lease term.Either one of these accomplishes everybody's goals without getting into messy technicalities that come about with a sublease.Most leases contain prohibitions against subleasing without the landlord's consent.Many leases charge a one-time fee if the tenant subleases, or is let out of their lease and a new tenant accepted.That is because the situation causes extra work and risk for the landlord. 

If your goal is to maximize your retirement plan contributions with a SEP, then keeping things as a basic LLC might be better.If you're really concerned about keeping your brokerage and your personal commissions separate, then two separate entities, possibly either 2 S-Corps or a nested S-Corp/LLC structure might be best.So when tax season is over, sit down with your CPA and outline your goals and your issues and see what they recommend.Now if what you've got is a data entry/"tax preparer" who simply enters your data into tax forms, consider switching providers. 

I'm a little concerned about the timing of moving out of my current renting situation and buying a new place, fixing it up, and renting it out. 

Going from $690 to $1000 may cause them to leave, which could impact you via vacancy expenses if those units aren't capable of demanding $1000.

Usually not lol but I learned a ton and wouldn't trade it for anything cause now I know what I'm talking about and can carry on a conversation with a contractor who can respect my opinion.That's my 2 cents.

Have talked to a few and they are willing to lend on the property, the concern is that with such a high commercial %  that MI company won't insure.   

If you cloud someones title on a scheme were you personally do not have the funds to close you could find yourself in a situation where you caused damage to the seller and your liable. also its prima facia evidence your selling real estate without a license..

My main concern with this unit is the 4 bedroom/2 full baths.   

Saturation of the market is one concern.